Photos of Leonardo DiCaprio Looking Like Frank Sinatra on the Cover of Esquire Magazine 2010-02-11 12:30:06

Leo Dishes His Top Ten Life Lessons to Esquire

Handsome Leonardo DiCaprio is looking cool as ever, with a glowing tan, slicked back hair and drink in hand on the March cover of Esquire. The actor's next film Shutter Island finally opens next week so he's reflecting on his impressive career and the life lessons he's learned along the way. Most of you think Leo would be the best choice to play Frank Sinatra in the upcoming Martin Scorsese biopic and judging by these photos he looks like he's already practicing for the part. Here's more:

Leo on River Phoenix: "When I was eighteen, River Phoenix was far and away my hero. Think of all those early great performances — My Own Private Idaho. Stand by Me. I always wanted to meet him. One night, I was at this Halloween party, and he passed me. He was beyond pale — he looked white. Before I got a chance to say hello, he was gone, driving off to the Viper Room, where he fell over and died. That's a lesson."

His earliest memories on stage: "The earliest memories I have are jumping up onstage before concerts in downtown L. A. and trying to get on the mic and break-dance, or do imitations of my mother's friends or my father's friends, or be a comic in class. I was the most insane child you can imagine, pretty intolerable to be around. High-octane energy all the time, never wanting to focus on schoolwork."

On what drives him to act: "Probably the only thing I knew with complete clarity was that I wanted to be an actor. But there was a lot of rejection early on, and so it never felt like, Hey, I've got something here. There was always an element of me that needed to prove something to myself. It's something I don't want to get rid of, because it's what drives me. I'm never settled and I'm never satisfied."

It makes me feel so damn old to see Leo looking so....well, old. haha. Still sexy though! Love that Leo. I always see his movies.

5 years

I think that people bring up River's death because he was such an outstanding actor, with a long career ahead of himself, and yet it was all over so fast due to chain of bad decisions...I think that is the lesson Leo is referring to (and I doubt he would have brought up his death, had he not been asked to detail a few of the life lessons he has learned throughout his tenure in the movies). Leo has had a long career and it will continue because he hasn't let the so-called allure of hollywood (fame, sex, drugs, general sense of invincibility) pervade his being, as many talented stars do.

Why is it when people mention River Phoenix, they have to bring up his death? We get it, he died. Why couldnt he have said that he was his hero and leave it at that? I also dont think he has aged well.

He's 35. Why does he look like a California Raisin? Same with his nasty girlfriend. I'd like to know what their diets/lifestyles are like so I know what to avoid.

5 years

Great actor but not in the least bit attractive to me. Leo does seem like a nice guy though. I'm puzzled why he only dates vapid stupid models. Leo is a smart guy so it doesn't make sense. Oh well, I'm rooting for Leo to win an Oscar soon because he deserves it.